# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Wed Apr  1 17:55:04 2020
#   Inital geometry file: a 115 line input string
#   Ligand name: N-benzyl-4-[4-(3-chlorophenyl)-1H-pyrazol-3-yl]-1H-pyrrole-2-carboxamide
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: Clc1cccc(c1)c2c[nH]nc2c3c[nH]c(c3)C(=O)NCc4ccccc4
#
data_comp_list
loop_
_chem_comp.id
_chem_comp.three_letter_code
_chem_comp.name
_chem_comp.group
_chem_comp.number_atoms_all
_chem_comp.number_atoms_nh
_chem_comp.desc_level
_chem_comp.initial_date
_chem_comp.modified_date
_chem_comp.source
 33A  33A  N-benzyl-4-[4-(3-chlorophenyl)-1H-pyrazol-3-yl]-1H-pyrrole-2-carboxamide  ligand  44  27  .  2021-08-04  2021-08-04  
;
Directly from eLBOW using geometry from QM method PBEh-3c with CPCM solvent model
Validated by Mogul as PERFECT
;

data_comp_33A
loop_
_chem_comp_atom.comp_id
_chem_comp_atom.atom_id
_chem_comp_atom.type_symbol
_chem_comp_atom.type_energy
_chem_comp_atom.charge
_chem_comp_atom.partial_charge
_chem_comp_atom.x
_chem_comp_atom.y
_chem_comp_atom.z
 33A  C2    C   CR6   0  -0.020   8.9808  -1.9185  -3.1668
 33A  C3    C   CR16  0  -0.230  10.0907  -2.2596  -2.4117
 33A  C4    C   CR16  0  -0.241   9.8887  -2.8037  -1.1502
 33A  C5    C   CR16  0  -0.296   8.6084  -2.9990  -0.6591
 33A  C6    C   CR6   0   0.027   7.4939  -2.6398  -1.4195
 33A  C7    C   CR16  0  -0.279   7.6924  -2.0958  -2.6881
 33A  C8    C   CR5   0  -0.174   6.1341  -2.8427  -0.9115
 33A  CL1   CL  CL    0  -0.133   9.2045  -1.2379  -4.7474
 33A  C9    C   CR15  0   0.010   5.0812  -3.4239  -1.5871
 33A  N10   N   NR15  0  -0.428   4.0483  -3.4465  -0.7367
 33A  N12   N   N     0  -0.297   4.3301  -2.9118   0.4445
 33A  C13   C   CR5   0   0.247   5.5975  -2.5373   0.3665
 33A  C14   C   CR5   0  -0.016   6.2591  -1.8875   1.4890
 33A  C15   C   CR15  0  -0.051   6.0047  -2.1062   2.8316
 33A  N16   N   NR15  0  -0.620   6.8376  -1.3304   3.5514
 33A  C18   C   CR5   0   0.245   7.6307  -0.5958   2.7212
 33A  C19   C   CR15  0  -0.446   7.2902  -0.9233   1.4268
 33A  C20   C   C     0   0.491   8.6909   0.2635   3.2590
 33A  O21   O   O     0  -0.496   9.0335   0.1921   4.4340
 33A  N22   N   NH1   0  -0.654   9.2526   1.0967   2.3618
 33A  C23   C   CH2   0  -0.329  10.4717   1.8325   2.5825
 33A  C24   C   CR6   0   0.089  11.5162   1.5246   1.5356
 33A  C25   C   CR16  0  -0.293  11.6452   0.2486   0.9917
 33A  C26   C   CR16  0  -0.236  12.6223  -0.0199   0.0429
 33A  C27   C   CR16  0  -0.268  13.4884   0.9830  -0.3731
 33A  C28   C   CR16  0  -0.241  13.3676   2.2571   0.1652
 33A  C29   C   CR16  0  -0.306  12.3848   2.5249   1.1089
 33A  H3    H   HCR6  0   0.278  11.0901  -2.1088  -2.7961
 33A  H4    H   HCR6  0   0.265  10.7446  -3.0862  -0.5512
 33A  H5    H   HCR6  0   0.259   8.4708  -3.4374   0.3205
 33A  H7    H   HCR6  0   0.271   6.8433  -1.7999  -3.2910
 33A  H9    H   HCR5  0   0.294   5.0154  -3.8336  -2.5821
 33A  HN10  H   HNR5  0   0.424   3.1286  -3.8186  -0.9116
 33A  H15   H   HCR5  0   0.282   5.2995  -2.7674   3.3077
 33A  HN16  H   HNR5  0   0.415   6.8808  -1.3016   4.5581
 33A  H19   H   HCR5  0   0.260   7.7381  -0.5310   0.5275
 33A  HN22  H   HNH1  0   0.406   8.8459   1.1598   1.4425
 33A  H231  H   HCH2  0   0.272  10.8455   1.5733   3.5738
 33A  H232  H   HCH2  0   0.261  10.2726   2.9072   2.5963
 33A  H25   H   HCR6  0   0.243  10.9759  -0.5446   1.3021
 33A  H26   H   HCR6  0   0.252  12.7070  -1.0161  -0.3730
 33A  H27   H   HCR6  0   0.256  14.2492   0.7752  -1.1143
 33A  H28   H   HCR6  0   0.256  14.0337   3.0476  -0.1560
 33A  H29   H   HCR6  0   0.253  12.2899   3.5258   1.5140

loop_
_chem_comp_bond.comp_id
_chem_comp_bond.atom_id_1
_chem_comp_bond.atom_id_2
_chem_comp_bond.type
_chem_comp_bond.value_dist
_chem_comp_bond.value_dist_esd
_chem_comp_bond.value_dist_neutron
 33A  C2   CL1   single    1.735  0.020  1.735
 33A  C2   C7    aromatic  1.386  0.020  1.386
 33A  C2   C3    aromatic  1.385  0.020  1.385
 33A  C3   C4    aromatic  1.389  0.020  1.389
 33A  C3   H3    single    0.930  0.020  1.080
 33A  C4   C5    aromatic  1.385  0.020  1.385
 33A  C4   H4    single    0.930  0.020  1.080
 33A  C5   C6    aromatic  1.396  0.020  1.396
 33A  C5   H5    single    0.930  0.020  1.080
 33A  C6   C7    aromatic  1.395  0.020  1.395
 33A  C6   C8    single    1.466  0.020  1.466
 33A  C7   H7    single    0.930  0.020  1.080
 33A  C8   C13   aromatic  1.419  0.020  1.419
 33A  C8   C9    aromatic  1.379  0.020  1.379
 33A  C9   N10   aromatic  1.338  0.020  1.338
 33A  C9   H9    single    0.930  0.020  1.080
 33A  N10  N12   aromatic  1.327  0.020  1.327
 33A  N10  HN10  single    0.860  0.020  1.020
 33A  N12  C13   aromatic  1.324  0.020  1.324
 33A  C13  C14   single    1.456  0.020  1.456
 33A  C14  C15   aromatic  1.384  0.020  1.384
 33A  C14  C19   aromatic  1.413  0.020  1.413
 33A  C15  N16   aromatic  1.347  0.020  1.347
 33A  C15  H15   single    0.930  0.020  1.080
 33A  N16  C18   aromatic  1.363  0.020  1.363
 33A  N16  HN16  single    0.860  0.020  1.020
 33A  C18  C20   single    1.467  0.020  1.467
 33A  C18  C19   aromatic  1.378  0.020  1.378
 33A  C19  H19   single    0.930  0.020  1.080
 33A  C20  O21   double    1.226  0.020  1.226
 33A  C20  N22   single    1.347  0.020  1.347
 33A  N22  C23   single    1.441  0.020  1.441
 33A  N22  HN22  single    0.860  0.020  1.020
 33A  C23  C24   single    1.511  0.020  1.511
 33A  C23  H231  single    0.970  0.020  1.090
 33A  C23  H232  single    0.970  0.020  1.090
 33A  C24  C25   aromatic  1.393  0.020  1.393
 33A  C24  C29   aromatic  1.392  0.020  1.392
 33A  C25  C26   aromatic  1.388  0.020  1.388
 33A  C25  H25   single    0.930  0.020  1.080
 33A  C26  C27   aromatic  1.389  0.020  1.389
 33A  C26  H26   single    0.930  0.020  1.080
 33A  C27  C28   aromatic  1.388  0.020  1.388
 33A  C27  H27   single    0.930  0.020  1.080
 33A  C28  C29   aromatic  1.389  0.020  1.389
 33A  C28  H28   single    0.930  0.020  1.080
 33A  C29  H29   single    0.930  0.020  1.080

loop_
_chem_comp_angle.comp_id
_chem_comp_angle.atom_id_1
_chem_comp_angle.atom_id_2
_chem_comp_angle.atom_id_3
_chem_comp_angle.value_angle
_chem_comp_angle.value_angle_esd
 33A  CL1   C2   C7    118.99  3.000
 33A  C7    C2   C3    121.67  3.000
 33A  CL1   C2   C3    119.33  3.000
 33A  H3    C3   C4    120.80  3.000
 33A  H3    C3   C2    120.82  3.000
 33A  C4    C3   C2    118.38  3.000
 33A  H4    C4   C5    119.87  3.000
 33A  H4    C4   C3    119.35  3.000
 33A  C5    C4   C3    120.78  3.000
 33A  H5    C5   C6    119.72  3.000
 33A  H5    C5   C4    119.71  3.000
 33A  C6    C5   C4    120.56  3.000
 33A  C8    C6   C7    120.09  3.000
 33A  C8    C6   C5    121.08  3.000
 33A  C7    C6   C5    118.83  3.000
 33A  H7    C7   C6    120.10  3.000
 33A  H7    C7   C2    120.12  3.000
 33A  C6    C7   C2    119.77  3.000
 33A  C13   C8   C9    104.07  3.000
 33A  C9    C8   C6    126.63  3.000
 33A  C13   C8   C6    129.27  3.000
 33A  H9    C9   N10   122.21  3.000
 33A  H9    C9   C8    131.20  3.000
 33A  N10   C9   C8    106.56  3.000
 33A  HN10  N10  N12   119.82  3.000
 33A  HN10  N10  C9    126.92  3.000
 33A  N12   N10  C9    113.26  3.000
 33A  C13   N12  N10   105.36  3.000
 33A  C14   C13  N12   121.05  3.000
 33A  C14   C13  C8    128.20  3.000
 33A  N12   C13  C8    110.74  3.000
 33A  C19   C14  C15   106.54  3.000
 33A  C19   C14  C13   127.03  3.000
 33A  C15   C14  C13   126.43  3.000
 33A  H15   C15  N16   121.47  3.000
 33A  H15   C15  C14   130.24  3.000
 33A  N16   C15  C14   108.29  3.000
 33A  HN16  N16  C18   124.61  3.000
 33A  HN16  N16  C15   125.22  3.000
 33A  C18   N16  C15   110.16  3.000
 33A  C20   C18  C19   131.47  3.000
 33A  C19   C18  N16   107.48  3.000
 33A  C20   C18  N16   120.86  3.000
 33A  H19   C19  C18   126.45  3.000
 33A  H19   C19  C14   126.01  3.000
 33A  C18   C19  C14   107.53  3.000
 33A  N22   C20  O21   123.90  3.000
 33A  N22   C20  C18   114.81  3.000
 33A  O21   C20  C18   121.28  3.000
 33A  HN22  N22  C23   116.71  3.000
 33A  HN22  N22  C20   118.57  3.000
 33A  C23   N22  C20   124.52  3.000
 33A  H232  C23  H231  106.54  3.000
 33A  H232  C23  C24   109.58  3.000
 33A  H231  C23  C24   110.15  3.000
 33A  H232  C23  N22   110.48  3.000
 33A  H231  C23  N22   107.92  3.000
 33A  C24   C23  N22   112.01  3.000
 33A  C29   C24  C25   118.74  3.000
 33A  C29   C24  C23   119.83  3.000
 33A  C25   C24  C23   121.42  3.000
 33A  H25   C25  C26   119.28  3.000
 33A  H25   C25  C24   120.10  3.000
 33A  C26   C25  C24   120.61  3.000
 33A  H26   C26  C27   120.03  3.000
 33A  H26   C26  C25   119.71  3.000
 33A  C27   C26  C25   120.26  3.000
 33A  H27   C27  C28   120.19  3.000
 33A  H27   C27  C26   120.32  3.000
 33A  C28   C27  C26   119.49  3.000
 33A  H28   C28  C29   119.76  3.000
 33A  H28   C28  C27   120.10  3.000
 33A  C29   C28  C27   120.14  3.000
 33A  H29   C29  C28   119.60  3.000
 33A  H29   C29  C24   119.64  3.000
 33A  C28   C29  C24   120.76  3.000

loop_
_chem_comp_tor.comp_id
_chem_comp_tor.id
_chem_comp_tor.atom_id_1
_chem_comp_tor.atom_id_2
_chem_comp_tor.atom_id_3
_chem_comp_tor.atom_id_4
_chem_comp_tor.value_angle
_chem_comp_tor.value_angle_esd
_chem_comp_tor.period
 33A  CONST_01  C5    C6   C7   C2     0.00   0.0  0
 33A  CONST_02  C8    C6   C7   C2   180.00   0.0  0
 33A  CONST_03  C5    C4   C3   C2     0.00   0.0  0
 33A  CONST_04  C6    C7   C2   C3     0.00   0.0  0
 33A  CONST_05  C6    C5   C4   C3     0.00   0.0  0
 33A  CONST_06  C7    C2   C3   C4     0.00   0.0  0
 33A  CONST_07  C7    C6   C5   C4     0.00   0.0  0
 33A  CONST_08  C8    C6   C5   C4   180.00   0.0  0
 33A  CONST_11  N12   C13  C8   C6   180.00   0.0  0
 33A  CONST_12  C14   C13  C8   C6     0.00   0.0  0
 33A  CONST_13  N10   C9   C8   C6   180.00   0.0  0
 33A  CONST_16  N10   N12  C13  C8     0.00   0.0  0
 33A  CONST_19  N12   N10  C9   C8     0.00   0.0  0
 33A  CONST_20  N12   C13  C8   C9     0.00   0.0  0
 33A  CONST_21  C14   C13  C8   C9   180.00   0.0  0
 33A  CONST_22  C13   N12  N10  C9     0.00   0.0  0
 33A  CONST_23  C13   C8   C9   N10    0.00   0.0  0
 33A  CONST_24  C14   C13  N12  N10  180.00   0.0  0
 33A  CONST_27  N16   C15  C14  C13  180.00   0.0  0
 33A  CONST_28  C18   C19  C14  C13  180.00   0.0  0
 33A  CONST_29  C18   N16  C15  C14    0.00   0.0  0
 33A  CONST_30  N16   C18  C19  C14    0.00   0.0  0
 33A  CONST_31  C18   C19  C14  C15    0.00   0.0  0
 33A  CONST_32  C19   C18  N16  C15    0.00   0.0  0
 33A  CONST_33  C19   C14  C15  N16    0.00   0.0  0
 33A  CONST_34  C27   C26  C25  C24    0.00   0.0  0
 33A  CONST_35  C27   C28  C29  C24    0.00   0.0  0
 33A  CONST_36  C28   C29  C24  C25    0.00   0.0  0
 33A  CONST_37  C28   C27  C26  C25    0.00   0.0  0
 33A  CONST_38  C29   C24  C25  C26    0.00   0.0  0
 33A  CONST_39  C29   C28  C27  C26    0.00   0.0  0
 33A  CONST_40  CL1   C2   C3   C4   180.00   0.0  0
 33A  CONST_41  CL1   C2   C7   C6   180.00   0.0  0
 33A  CONST_42  C20   C18  C19  C14  180.00   0.0  0
 33A  CONST_43  C20   C18  N16  C15  180.00   0.0  0
 33A  CONST_44  C26   C25  C24  C23  180.00   0.0  0
 33A  CONST_45  C28   C29  C24  C23  180.00   0.0  0
 33A  CONST_46  H4    C4   C3   C2   180.00   0.0  0
 33A  CONST_47  H7    C7   C2   C3   180.00   0.0  0
 33A  CONST_48  H5    C5   C4   C3   180.00   0.0  0
 33A  CONST_49  H3    C3   C4   C5   180.00   0.0  0
 33A  CONST_50  H9    C9   C8   C6     0.00   0.0  0
 33A  CONST_51  HN10  N10  C9   C8   180.00   0.0  0
 33A  CONST_52  H15   C15  C14  C13    0.00   0.0  0
 33A  CONST_53  H19   C19  C14  C13    0.00   0.0  0
 33A  CONST_54  HN16  N16  C15  C14  180.00   0.0  0
 33A  CONST_55  H26   C26  C25  C24  180.00   0.0  0
 33A  CONST_56  H28   C28  C29  C24  180.00   0.0  0
 33A  CONST_57  H29   C29  C24  C25  180.00   0.0  0
 33A  CONST_58  H27   C27  C26  C25  180.00   0.0  0
 33A  CONST_59  H25   C25  C26  C27  180.00   0.0  0
 33A  CONST_60  C23   N22  C20  C18  180.00   0.0  0
 33A  CONST_61  HN22  N22  C20  C18    0.00   0.0  0
 33A  CONST_62  C23   N22  C20  O21    0.00   0.0  0
 33A  Var_01    O21   C20  C18  N16   11.51  30.0  2
 33A  Var_02    C25   C24  C23  N22  -35.44  30.0  2
 33A  Var_03    C24   C23  N22  C20  122.60  30.0  3

loop_
_chem_comp_plane_atom.comp_id
_chem_comp_plane_atom.plane_id
_chem_comp_plane_atom.atom_id
_chem_comp_plane_atom.dist_esd
 33A  plan-1  C6    0.020
 33A  plan-1  C8    0.020
 33A  plan-1  C9    0.020
 33A  plan-1  N10   0.020
 33A  plan-1  N12   0.020
 33A  plan-1  C13   0.020
 33A  plan-1  C14   0.020
 33A  plan-1  H9    0.020
 33A  plan-1  HN10  0.020
 33A  plan-2  C13   0.020
 33A  plan-2  C14   0.020
 33A  plan-2  C15   0.020
 33A  plan-2  N16   0.020
 33A  plan-2  C18   0.020
 33A  plan-2  C19   0.020
 33A  plan-2  C20   0.020
 33A  plan-2  H15   0.020
 33A  plan-2  HN16  0.020
 33A  plan-2  H19   0.020
 33A  plan-3  C2    0.020
 33A  plan-3  C3    0.020
 33A  plan-3  C4    0.020
 33A  plan-3  C5    0.020
 33A  plan-3  C6    0.020
 33A  plan-3  C7    0.020
 33A  plan-3  C8    0.020
 33A  plan-3  CL1   0.020
 33A  plan-3  H3    0.020
 33A  plan-3  H4    0.020
 33A  plan-3  H5    0.020
 33A  plan-3  H7    0.020
 33A  plan-4  C23   0.020
 33A  plan-4  C24   0.020
 33A  plan-4  C25   0.020
 33A  plan-4  C26   0.020
 33A  plan-4  C27   0.020
 33A  plan-4  C28   0.020
 33A  plan-4  C29   0.020
 33A  plan-4  H25   0.020
 33A  plan-4  H26   0.020
 33A  plan-4  H27   0.020
 33A  plan-4  H28   0.020
 33A  plan-4  H29   0.020
 33A  plan-5  C18   0.020
 33A  plan-5  C20   0.020
 33A  plan-5  O21   0.020
 33A  plan-5  N22   0.020
 33A  plan-5  C23   0.020
 33A  plan-5  HN22  0.020

